75089-92-8

Upstream product

• 55339-95-2 dimethyl dihydrocinnamoylphosphonate 
• 19493-09-5 Methylenetriphenylphosphorane 
• 147297-66-3 (S)-(+)-(E)-S-phenyl-S-(4-phenylbut-1-enyl)-N-(p-tolylsulfonyl)sulfoximine 
• 645-45-4 hydrocinnamic acid chloride 

Relevant academic research and scientific papers

New Synthesis and Hydroboration of Vinylphosphonates

The Arbuzov reaction of trimethyl and triethyl phosphites with acyl chlorides gave 1-oxoalkylphosphonates in 57-80percent yields.The Wittig reaction of the phosphonates with methylenetriphenylphosphorane gave vinylphosphonates in 25-59percent yields.Hydroboration of vinylphosphonates in oxolane gave 2-hydroxyethylphosphonates in 50-65percent yields.The procedure seems to be a good synthetic method to afford 1-alkyl-substituted 2-hydroxyethylphosphonates which have one more carbon atom than the starting 1-oxoalkylphosphonates.

Nucleophilic Addition-Elimination Reactions of N-(p-Tolylsulphonyl)vinylsulphoximines: Preparation of α-Methylene Nitriles and Phosphonates

Treatment of N-(p-tolylsulphonyl)vinylsulphoximines (1) with lithium cyanide in DMF at room temperature leads to efficient formation of α,β-unsaturated nitriles (3), via a Michael addition-proton transfer-elimination process, in which the polarity of the double bond is reversed.Analogous reaction with lithium dimethylphosphonate leads to β-dimethylphosphonyl sulphoximines (7), which are converted to α,β-unsaturated phosphonates (6) by treatment with NaOMe.